Brenda's Hall Pass

We never intended to fall in love, but the heart wants what the heart wants and so we did. When you work with someone closely over an extended length of time, it's only natural to get close, but we got too close. Funny thing is, Brenda worked remote, and lived two states away, but she had to come in 4 times a year for quarterly meetings and lets just say we hit it off pretty quickly. We continued on with a romantic and intimate relationship for a few years before the guilt finally built up enough that she ended the relationship. "I'm sorry Brian, but I can't do this anymore." I was crushed but also understood it was the best thing for both of us. Though we were deeply in love and would have done anything for one another, the one thing we both refused to do was end our current marriages.

We remained friends, best friends, and told each other EVERYTHING. Yeah we would talk about our sex lives, or lack there of. Conversations at times would include stories about our previous experiences with both our current spouses and also previous partners. Also sometimes we'd talk about our sexual fantasies and desires. As time went on, our conversations became more and more detailed in a sexual manner and once again we found ourselves occasionally having phone sex. Brenda and I still loved each other, still desired each other, and once again we were giving into desire via sexting and phone sex. I would typically initiate the sexual conversations asking questions about her experiences and what fantasies she still has. The sexual themed questions became more and more common. One question that would end up being a common talking point would also lead to something that would make or break our relationship sometime down the road.

"Okay Brenda, another for you."

I could practically hear Brenda rolling her eyes. "Okay Brian, what is your question this time?" She laughs.

"If we ever did end up together, and I gave you a hall pass for one night, with the condition being we both have to know the person, would you take advantage of the opportunity? And who would you choose?"

I didn't think she would actually say that she would take advantage of the opportunity, but if she did, I was 90% certain I knew who she'd pick. And I wasn't wrong. Without hesitation she blurted out, "Evan!"

I teased her a bit because I figured she'd say Evan, who was a vendor we both worked with at the company we worked for. We also became friends over time, though after Evan left the company he worked for, we all lost touch a bit.

From time to time I'd bring up the topic, but she usually would try to quickly change the subject.

As time went on, we hadn't any opportunities to be actually physical as life was getting in the way. Amongst the obstacles in our lives, my wife was battling several autoimmune diseases and Brenda's husband had some heart issues and some neurological issues that he never cared to get diagnosed. Life became difficult for both of us as we often had to take care of the other ones we loved and truly belonged to.

Bobby, Brenda's husband, ended up having a severe stroke and sadly passed away shortly there after. It was very hard on her and their sons and I tried to be there as a friend as much as I could. However it wasn't long before my wife, Marcy, lost her battle too. It messed me up. We never had any children, and I always took for granted how much Marcy did as far as our finances went. Not only did I just lose my wife, a woman I loved deeply for most of my life, but I also had to figure out how to survive financially on my own now and how and when to pay all the bills. Needless to say, neither Brenda nor I were in a place where we could reconnect right away.

Some time had passed and we were both getting used to our new lives when I made time to go visit her. It was awkward at first because it had been so long since we had seen each other but before too long it felt like no time had passed at all. By then she was working for another company and was unable to work remote so I had asked my boss if I could work remote so I could move to another state. There wasn't anything keeping me in the office really so he agreed as long as I came in quarterly or as needed, since sometimes the warehouse needed help.

At first I moved to an apartment close to her house, but before too long I was moving in with her. Though both of us were no spring chickens, we were making love constantly. Maybe 3 times a week on weeknights and twice a day on the weekends! And even if I wasn't able to ever be intimate with Brenda, the fact I was able to be with her, to live with her, I was the happiest man alive, and I did everything in my power to make sure she was just as happy.

Just like with any relationship, as hot as it starts, the intimacy cools down, at least to an extent. I don't know if we got bored necessarily, but it did almost become too, I don't know, routine? I didn't mind, I still loved Brenda more than anything and I still enjoyed the sex, even if it wasn't as electric as it had previously been. But what bothered me is I felt like Brenda was getting bored with our sex life. Our love making didn't make her happy as it use to, and all I wanted to do was to make her happy, no matter what it took. So I brought that old topic up...

"Hey Brenda, remember that... scenario I brought up a while back? About the hall pass and Evan?" I asked nervously.

She rolled her eyes, sighed, and answered with an annoyance in her voice, "you never let me forget it, of course I remember. Why are you bringing it up now?"

"Well, what do you think about it? Would you do it? If he was okay with it, would you be?" I asked.

"Look at me, I doubt he'll want to" she said, never seeing what everyone else saw in her. She continued, "I mean, it would be fun, but why are you pushing for this?"

I didn't want to be turned on by the thought of it, but I already was. But I couldn't let Brenda know that. So the answer I gave wasn't the complete truth, though there was some truth behind it, "I just want you to have fun. I want you to be happy. I think one night with a man you've been attracted to for this long, might bring you a joy that you haven't experienced in a while. I want to set it up for you. But there's one condition.."

Brenda interrupted me, "whoa whoa whoa, I'm not sure I actually want this, do I?"

I walked over to her, gave her a hug and gave her a deep passionate kiss. I didn't want to pull away, since I still loved making out with her and the feeling of her breasts on my chest was always a turn on, but I had to answer her question and finish what I was going to say. "Brenda, if you're asking 'do I', then we both already know the answer." I held a finger to her lips to shush her so I could finish before she objected. "The only thing I ask in return, is that you give me details. And you answer any question I have about that night, and you answer truthfully."

There was silence for what seemed like hours, though it was probably about a single minute.

She finally spoke after clearing her voice, "I'm okay with it, I guess. Obviously only if you're okay with it. I still don't understand completely why you'd push for this, I'm suppose to be yours, but I can't deny it does sound fun. You really think he'll go for it?"

I was already getting excited and half hard, but I tried to contain my excitement while answering. "I'll reach out to Evan. I won't bring it up right away but I'll eventually ask and see what he says."

And with that I grabbed her hand and led her to the bedroom. I threw her on the bed, practically ripped her clothes off and passionately made love to her, like we haven't in some time. She was wetter than almost anytime I could ever remember, and her moans were louder. I knew she was definitely okay with the hall pass.

The next morning, while at work, I messaged Evan on instant messenger, "Hey Evan, long time no talk, how are things?"

We went back and forth a little, catching up with this and that, then I just called him over the phone and asked, "How's the dating life? Any girlfriends or anything?"

Evan laughed, "nah, still go on a date every now and again but I can just never settle down again. The ex-wife scarred me pretty bad, ya know?"

I laughed back and answered, "yeah I do know. It's a shame, you're one of the best dude's I know. Anyway, since we last talked, a lot has changed in my life. For starters, my wife passed a couple of years ago."

Evan immediately interrupted, "oh man, I'm so sorry. How have you been holding up?"

This next part took him for a surprise, "well, things have been easier since I now live with my girlfriend, Brenda."

"WHAT?!" Evan shouted through the phone.

"Haha, didn't expect that? Yeah, truth be told, we always had a thing for one another. Both of our spouses passed and so we just ended up with each other. But Evan, that's not the craziest thing you're about to hear over this conversation."

Evan was quiet at first, then laughed a little before coming to his senses and asking, "haha okay we'll see about that, what could be possibly crazier than that?"

I took a deep breath before continuing because this was the moment of truth, "Evan, I know you and Brenda had a thing with each other." He tried to say something but I cut him off and continued, "I know nothing ever happened between the two of you or anything like that, but I know there was an attraction. I know about some of the conversations you guys would have and I heard you guys flirt over the phone. And no it doesn't bother me, that's not why I'm bringing this up."

Evan asked, "okay sooo, what is this about then?"

I was grinning from ear to ear as I continued on, "Brenda and I have been talking a lot about this and she's getting a 1 night 'hall pass'. She could choose anyone who she wants to spend the night with, as long as I know who the person is too. And Evan, I was not surprised when she chose you. So yes, I'm offering you to have my wife for a night. That is, if you are willing to spend the time with her."

There was dead silence for a few seconds before he cleared his throat and spoke, "so you're saying I can have sex, with your girlfriend, Brenda, for one night? And you're both okay with this?" I shook my head silently and before I could actually answer over the phone, Evan answered, "It's weird man. It's damn weird, but uh... yeah, there's no way I'm turning this opportunity down."

We shared an awkward laugh, mine out of relief, his out of nervousness. We wrapped up our conversation, and I'm sure his brain was going a mile a minute, just as mine was.

Over the coming days and weeks, Evan and myself planned out some details, as far as date, time, and where the meet-up would take place. Evan lived 3 states away, so Brenda and I would use some PTO and make the drive and get a hotel near his house, where Evan would pick her up and drop her back off the following day. During the weeks leading up to the big evening, Brenda and Evan started texting and talking again. Catching up on their lives, and a lot of flirting, I'm sure. I wasn't ever around when they talked on the phone and I didn't ask what they texted about, but I imagine much of it was about what was about to happen.

The day was finally approaching and Brenda and I hopped into our Nissan and started the 10 hour trip. Because check-in was 1pm and I didn't feel like leaving in the middle of the night, we made hotel reservations at the half way point. The approximate 5 hour drive that day was quiet. We didn't speak about Evan or what was going to happen the following day. The conversations just entailed small chit chat and not much else. I think we were both pretty nervous. We held hands briefly during the drive but that's about as intimate as we got. We arrived at a small town and we had dinner and then some drinks at the hotel bar. The 2 double Maker's Mark on the rocks, and then the final one, neat, helped me relax and I started to get horny. We went back up to the room, and... nothing happened. Brenda wasn't in the mood. I guess she had too much on her mind with everything going on the next day but I was a little irritated. I let it go and we went to sleep, the drinks helped me fall asleep fast.

We woke up early the next day as we had to be out by 8am at the latest. I really wanted to get to the hotel at 1 exactly because Evan was going to pick Brenda up at 3 and I wanted to relax and allow Bredna enough time to get ready, if she needed it. So we got on the road by 8 and we stopped to get McDonald's breakfast on the way. Just like the previous day, the talk was small chit chat but something felt different this time. We were both excited and you could tell. Brenda wouldn't admit it, but she was. Our conversations were much more lively and a bit flirty even, much more so than the previous day.

We got to the hotel just a little after 1. We checked in and and brought our bags up to our room. As soon as we got up there and set our bags down, Brenda immediately started texting someone and was smiling quite a bit. I gotta admit, it started bothering me a little. I was getting jealous. She was going to be spending all night with Evan, but right now she was in the room with me, and I just wanted some attention. After all, I was the one allowing this.

She got done texting and plugged her phone into the table next to the bed. She grabbed her bag, walked to me, gave me a peck on the lips, then quickly disappeared into the bathroom. I was left there with my thoughts, and not much else. I thought about looking at her phone but I refrained. I turned on the tv and tried to distract myself while I waited for her to come out of the bathroom. I waited, and waited, and waited. I did hear the shower turn on and a hair dryer, but other than that, I heard nothing, for over an hour. It was about 2:45 when she finally came out. My jaw dropped. She was wearing a new dress and her make-up was done up more than usual. I couldn't take my eyes off of her, in that new black and red dress that was form fitting and sexy, but also classy and not too revealing. It might have been the best she's ever looked. My cock twitched. But something was wrong. As good as she looked, her face revealed that she wasn't happy. Was she having second thoughts? I spoke first, "Brenda, you look amazing. I'm jealous that you don't dress like this for me!" I laughed. "But, what's wrong? Why do you look upset?"

She looked up at me, almost looked like she had tears in her eyes but she did manage to let out a small laugh and said, "B, I don't need to dress like this for you. I can walk into a room wearing rags and you'll get turned on." She wasn't wrong. She continued. "I'm not sure Evan will find me that attractive so I have to try a little harder." She WAS wrong that time. "But nothing is wrong. I'm fine. Nothing is wron.." her voice faded away and she looked down.

I jumped up to my feet and held both of her hands and looked directly into her eyes. "Brenda, are you okay?"

"Brian, I don't know if I want to do this. And are you sure you even want me to do this?"

Before she could say another word, I pressed my lips to hers and my tongue darted into her mouth, greeting hers for a brief moment. I grabbed her ass and pressed her against my now fully hard cock. I lifted the dress and only then did I break my kiss to look down at her new red lace panties. I couldn't believe how sexy they were and how sexy she was. I just stared down and her crotch while feeling the lace with my hands on her ass. She laughed, titled my head up and said, "I'm serious, we can cancel this and I can stay here and we can just spend time together. I just don't know if I want this." I knew she did, but she was afraid I didn't want her to go through with it. But I wanted this for her. And I wanted to hear all about it the next day.

I kept my right hand on her thick ass and took my left hand and moved it around to the front and slipped my hand inside her new sexy panties, and easily slid a finger in. She was soaked. She let out a low moan, "uhhhh, B."

My finger gently moved in slow circles around her swollen clit. It took seconds before my hand was practically soaked, and I kept moving my finger while I spoke softly, "Brenda, baby, you're clearly excited about seeing Evan. You want this, and I want this for you." I moved my finger from her clit and drove it, along with another finger, deeper into her soaked pussy. She laughed, grabbed my arm, and removed my hand from her pussy and panties all together.

She looked into my eyes this time, flush in the face and a huge smile, "okay B, you're right. I'm looking forward to this, but he's going to be here any second and I don't want to be too messy before he picks me up."

Well that was frustrating, but I understood why she said that. Still, I needed some love. I pushed her against the wall and kissed her deeply. Her dress had moved back down into place and this time, instead of reaching for her, I pulled my cock out and brought her hand to it. She started stroking me and we were both moaning into each other's mouths when her phone vibrated. She pushed me away, and sounded irritated with me when she said, "see, I told you, he'll be here soon and you're trying to make me messy. Stop. I gotta get going."

"Fuck" I whispered to myself as I put my cock back into my shorts. Brenda walked over to her phone and picked it up.

"Yeah, he's here, waiting in the parking lot. I have to go" she said matter of factly. She grabbed her purse and quickly started walking towards the door. I basically had to run and grab her arm and turn her around for her to stop from just leaving so unceremoniously.

"Hey, you could say goodbye you know." I said with a smile on my face so she knew I wasn't actually upset.

She laughed, gave me a deep kiss and said, "I'm sorry. I'm so nervous, I don't know what I'm doing. You're still sure about this?"

"I grabbed her big left breast, just because, gave her a kiss back and said, "yeah, your nipple is begging to be let out of this dress, I think your whole body wants this. Again, I want this for you. I love you more than anything, Brenda."

"I love you too, Brian. Thank you for this. I'll see you in the morning." She gave me a peck on the cheek this time, and left without another word.

After she walked out, I walked to the window and pulled aside the blinds and looked out. I saw a red pick-up truck running near the hotel entrance. I assumed it was Evan. I watched my beautiful girlfriend walk out of the hotel and walk up to the truck. Evan did in fact get out to greet her. He gave her a hug. I was curious if they would kiss right off the bat, but after the quick hug, he held the door open for her and she got in. He eyed her up and down as she entered the truck, but she had no idea. He closed the door, got around the drivers side, got in and they drove away.

I was there alone in my room, my heart pounding, my eyes starting to tear up, and my cock still extremely hard. I basically had blue balls at this point. My balls hurt, my stomach hurt, I was ready to cry, and my mind was in a hundred places at once. I was sick to my stomach but horny as hell. Did I do the wrong thing? Right now it felt like I did.

Well first things first, I needed a release. So I went to the bathroom and stroked my cock for about 6 seconds before I shot my load, aiming it right into the toilet so that I didn't have to clean up a mess. It was one of the most disappointing and unceremonious orgasms I ever had. It was frustrating and disappointing but at last my thoughts were clear.

But now what was I going to do for the next 18 hours? It was just after 3, and I was getting hungry, but I was afraid to go out to eat at any restaurant in fear of seeing them together. I assumed he would take her out to eat before heading back to his place, so I ordered in. I ordered a pizza from a local place. I had the tv on but I mostly scrolled through various social media sites while I waited for the pizza to arrive. Though I felt super hungry when I ordered the pizza, and I should have eaten a lot, after two small slices, I lost my appetite. I was nervous. I kept thinking about and imagining what was happening. It was weird how it both bothered me and excited me at the same time. And it was only 5pm by the time I stopped eating and closed up the pizza box.